FIELD OF THE INVENTION
This invention is directed to a new process for organic compounds and is particularly concerned with a process for the production of 1-[(amino or substituted amino)methyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines as well as with the new intermediates III and IV in this process.
The process of production and the novel intermediates can be illustratively represented as follows: ##SPC5## ##SPC6## ##SPC7##
Wherein R'.sub.o is alkyl; and wherein the rings A and B are unsubstituted or substituted by one or two substituents selected from the group consisting of chloro, fluoro, bromo, nitro, and trifluoromethyl.
The more important intermediates have the formulae IIIA and IVA below: ##SPC8##
And ##SPC9##
Wherein R.sub.1 is hydrogen, chloro or fluoro; wherein R.sub.2 is hydrogen, or fluoro when R.sub.1 is fluoro; and wherein R.sub.3 is hydrogen, chloro, fluoro, or trifluoromethyl.
The most important intermediates are of the formula IIIB and IVB below. ##SPC10##
And ##SPC11##
Wherein R'.sub.1 and R'.sub.3 are hydrogen or chlorine.
The process of this invention comprises: reacting a compound of formula I with formic acid and acetic anhydride at 0.degree. to 25.degree. to obtain compound II; and then warming the resulting mixture at 90.degree. to 118.degree.; heating a compound of formula II with paraformaldehyde in an inert organic solvent between 118.degree. and 150.degree. C. to obtain compound III; treating compound III with phthalimide, triphenylphosphine, and diethyl azodicarboxylate between 0.degree. to 35.degree. C, to obtain compound IV; treating IV with hydrazine hydrate at 60.degree. - 100.degree. C. in an alkanol of 1 to 3 carbon atoms, inclusive, to obtain compound V; and alkylating compound V with a carboxaldehyde of 1 to 3 carbon atoms inclusive, sodium cyanoborohydride and acetic acid to obtain a compound of formula VI above.